How many roads must a woman walk down before someone gives her a seat on the bus? Yes, and how many times must a woman be patronised by shop assistants who direct her towards the “mature and stylish” section before she is legally allowed to wallop them with her handbag? Yes, and how many times must a woman complain there is nothing decent in stores for women aged between 45 and 75 before anything changes? The answers, my friend, are, respectively, 17, four and infinity. Seventeen, four and infinity.

I have written many times about how stupid it is that the fashion industry directs the vast majority of its attention on the young and the thin when older women generally have more money to spend. So many times, in fact, that I think if I go there again my laptop might throw itself out the window out of utter boredom. But the point is, most clothes are manufactured with pretty twentysomethings in mind, which does rather lead to a glut of cutesy stuff on sale. You know, jumpers with punning slogans on them (clothes are made to be worn, not read), or blouses decorated with images of fruit, or shoes with animal faces on them.

Animals with what, you ask? Oh take me by the hand, people, while I share a story from the coalface of fashion shopping. A few weeks ago, a friend invited me to a secondhand designer fashion sale for charity, which sounded great but actually turned out to be a massive waste of time because most rich people’s clothes are gross. But, as I was leaving, I spotted the Charlotte Olympia stall. Charlotte Olympia is a young British brand that makes, by and very large, lovely high-heeled shoes. Ridiculous ones, of course – as all high heels are ridiculous, given that they are torture instruments for women legitimised by society – but, still, they are lovely to look at. All these shoes were being sold at such a ridiculous fraction of their price that I thought I should at least browse. And, incredibly, I found some flat shoes that were pretty and so cheap you couldn’t find shoes in Zara at that price. But here’s the thing: they had the picture of a cat’s face on the toe of each shoe.

Is this acceptable? Well, if you’re five, sure. I am not five. But I am my grandmother’s granddaughter and cannot resist a bargain, so I bought them, wore them the next day to work and spent the whole day asking my colleagues: “Are these too cute? Are they? Tell me honestly. Are they?” It really is testament to my colleagues’ stamina that they didn’t rip the shoes off my feet and shove them down my throat just to shut me up. So here’s my tuppence worth (tuppence is a cute word, if there ever was one). I definitely don’t think any woman should ever feel she’s too old for something, however cute or not cute. Live a little! Knock yourself out with that flamingo-print blouse! But if wearing something makes you so self-conscious that you drive your colleagues around the twist by seeking validation from them, then it’s probably not for you. Cuteness is in the eye of the wearer, and the wearer’s eye is all that matters.

Nobody should ever be in possession of a Hermès handbag if they can’t even spell ‘handbag’. Photograph: Bobby Yip/Reuters

How many handbags is too many handbags? My girlfriend has 17 – I counted! – and she’s asked for another for her birthday. Isn’t this ridiculous?

Dan, by email

Ladies and their handbags – amirite?! Spend that much on a bag and you won’t have any money to put in the bag! Good thing you’re around, Dan, to police your girlfriend’s possessions and count them in a totally non-creepy way – where would she be without you? Yes, a lot of women like handbags. A lot of men love trainers, watches, suits – all manner of things, really. How many sports matches have you been to, Dan? Why bother? They’re all on TV, and in every match someone wins and someone loses or they tie – who cares? That’s right, buddy boy, two can play at this game.

As it happens, I love handbags and I’ve read quite a lot of nonsense in my time about how a woman’s handbag is her substitute baby, or an externalistion or her womb, and all sorts of Freudian bollocks, all invariably written by men. To which I say, if anyone spots a baby covered in the Louis Vuitton logo please do tell me as I would totally adopt that baby. Your girlfriend asked for a handbag for her birthday, so give her a damn handbag. What kind of monster judges someone’s birthday request?

But in answer to your question, yes, it is possible for a woman to have too many handbags, and that woman is Tamara Ecclestone. I recently watched a video in which Tamara gave a tour of her “spring/summer closet”, which was essentially a recruitment video for the Communist party. Among the many, many, many revolting revelations in this video, including that she lives in only four rooms in her 57-room house, was Tamara’s “handbag shelves”, which, as the presenter rightly said, looked like the Chanel store.

But the real kicker was that Tamara and her three-year-old daughter have matching personalised Hermès Birkin bags. Vive la revolution! So there are two people who have too many handbags, both Tamara and her daughter (because if you’re going to have a five-figure handbag, you should at least be able to spell the word “handbag”). Everyone else, though, is under the limit. Especially, Dan, your girlfriend.